CH675418A5 - - Google Patents
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- Publication number
- CH675418A5 CH675418A5 CH195/87A CH19587A CH675418A5 CH 675418 A5 CH675418 A5 CH 675418A5 CH 195/87 A CH195/87 A CH 195/87A CH 19587 A CH19587 A CH 19587A CH 675418 A5 CH675418 A5 CH 675418A5
- Authority
- CH
- Switzerland
- Prior art keywords
- found
- calculated
- elemental analysis
- carbonyl
- piperazine
- Prior art date
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 223
- 238000000034 method Methods 0.000 claims description 45
- 150000001412 amines Chemical class 0.000 claims description 15
- 239000002664 nootropic agent Substances 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 12
- WGOIHPRRFBCVBZ-VKHMYHEASA-N (2s)-5-oxopyrrolidine-2-carboxamide Chemical class NC(=O)[C@@H]1CCC(=O)N1 WGOIHPRRFBCVBZ-VKHMYHEASA-N 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- ODHCTXKNWHHXJC-GSVOUGTGSA-N 5-oxo-D-proline Chemical class OC(=O)[C@H]1CCC(=O)N1 ODHCTXKNWHHXJC-GSVOUGTGSA-N 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- WGOIHPRRFBCVBZ-GSVOUGTGSA-N (2r)-5-oxopyrrolidine-2-carboxamide Chemical class NC(=O)[C@H]1CCC(=O)N1 WGOIHPRRFBCVBZ-GSVOUGTGSA-N 0.000 claims description 4
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 216
- 238000000921 elemental analysis Methods 0.000 description 107
- 150000001875 compounds Chemical class 0.000 description 76
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 58
- -1 piperazino Chemical group 0.000 description 42
- 230000000694 effects Effects 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 27
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 241001465754 Metazoa Species 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 19
- 239000003795 chemical substances by application Substances 0.000 description 19
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 239000000825 pharmaceutical preparation Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 229960000793 aniracetam Drugs 0.000 description 10
- ZXNRTKGTQJPIJK-UHFFFAOYSA-N aniracetam Chemical compound C1=CC(OC)=CC=C1C(=O)N1C(=O)CCC1 ZXNRTKGTQJPIJK-UHFFFAOYSA-N 0.000 description 10
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- 229930000680 A04AD01 - Scopolamine Natural products 0.000 description 9
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- STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 9
- 241000700159 Rattus Species 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 9
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
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- 125000001424 substituent group Chemical group 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- 239000002253 acid Substances 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- GOWRRBABHQUJMX-UHFFFAOYSA-N fasoracetam Chemical compound C1CCCCN1C(=O)C1CCC(=O)N1 GOWRRBABHQUJMX-UHFFFAOYSA-N 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 208000024891 symptom Diseases 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 150000008282 halocarbons Chemical class 0.000 description 5
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- 239000007858 starting material Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- MDMAUEITTFGEIK-UHFFFAOYSA-N 5-(piperazine-1-carbonyl)pyrrolidin-2-one Chemical compound C1CNCCN1C(=O)C1CCC(=O)N1 MDMAUEITTFGEIK-UHFFFAOYSA-N 0.000 description 4
- 206010010904 Convulsion Diseases 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 230000036461 convulsion Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 239000002798 polar solvent Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 150000001350 alkyl halides Chemical class 0.000 description 3
- 238000007112 amidation reaction Methods 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 238000010171 animal model Methods 0.000 description 3
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
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- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 3
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- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
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- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
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- 125000005505 thiomorpholino group Chemical group 0.000 description 3
- ULSDMUVEXKOYBU-ZDUSSCGKSA-N zolmitriptan Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1C[C@H]1COC(=O)N1 ULSDMUVEXKOYBU-ZDUSSCGKSA-N 0.000 description 3
- JEOVABNPJMHXGZ-QMMMGPOBSA-N (2S)-5-oxo-1-piperidin-1-ylpyrrolidine-2-carboxamide Chemical class NC(=O)[C@@H]1CCC(=O)N1N1CCCCC1 JEOVABNPJMHXGZ-QMMMGPOBSA-N 0.000 description 2
- YQXLOVXVWICTBX-ZETCQYMHSA-N (2S)-5-oxo-1-pyrrolidin-1-ylpyrrolidine-2-carboxamide Chemical class NC(=O)[C@@H]1CCC(=O)N1N1CCCC1 YQXLOVXVWICTBX-ZETCQYMHSA-N 0.000 description 2
- LCXSXBYYVYTYDY-BTJKTKAUSA-N (z)-but-2-enedioic acid;piperazine Chemical compound C1CNCCN1.OC(=O)\C=C/C(O)=O LCXSXBYYVYTYDY-BTJKTKAUSA-N 0.000 description 2
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- IIGFRCNOTWWJGY-UHFFFAOYSA-N 5-[4-(2-chlorophenyl)piperazine-1-carbonyl]pyrrolidin-2-one Chemical compound ClC1=CC=CC=C1N1CCN(C(=O)C2NC(=O)CC2)CC1 IIGFRCNOTWWJGY-UHFFFAOYSA-N 0.000 description 2
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- GOWRRBABHQUJMX-MRVPVSSYSA-N Fasoracetam Chemical compound C1CCCCN1C(=O)[C@H]1CCC(=O)N1 GOWRRBABHQUJMX-MRVPVSSYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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- 208000006011 Stroke Diseases 0.000 description 2
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- 150000008065 acid anhydrides Chemical class 0.000 description 2
- ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 description 2
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
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- ZULJGOSFKWFVRX-UHFFFAOYSA-N pramiracetam Chemical compound CC(C)N(C(C)C)CCNC(=O)CN1CCCC1=O ZULJGOSFKWFVRX-UHFFFAOYSA-N 0.000 description 2
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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- LUZOFMGZMUZSSK-LRDDRELGSA-N (-)-indolactam V Chemical compound C1[C@@H](CO)NC(=O)[C@H](C(C)C)N(C)C2=CC=CC3=C2C1=CN3 LUZOFMGZMUZSSK-LRDDRELGSA-N 0.000 description 1
- LLZWOOMWJQIHAW-ZETCQYMHSA-N (2S)-1-morpholin-4-yl-5-oxopyrrolidine-2-carboxamide Chemical compound O1CCN(CC1)N1[C@@H](CCC1=O)C(=O)N LLZWOOMWJQIHAW-ZETCQYMHSA-N 0.000 description 1
- IGUYYHAFNYFSEJ-GFCCVEGCSA-N (5R)-5-[4-(2-morpholin-4-yl-2-oxoethyl)piperazine-1-carbonyl]pyrrolidin-2-one Chemical compound C1COCCN1C(=O)CN(CC1)CCN1C(=O)[C@H]1CCC(=O)N1 IGUYYHAFNYFSEJ-GFCCVEGCSA-N 0.000 description 1
- JIICDYRNQKVXFR-OAHLLOKOSA-N (5R)-5-[4-[(4-methylphenyl)methyl]piperazine-1-carbonyl]pyrrolidin-2-one Chemical compound C1=CC(C)=CC=C1CN1CCN(C(=O)[C@@H]2NC(=O)CC2)CC1 JIICDYRNQKVXFR-OAHLLOKOSA-N 0.000 description 1
- WPDJMBAXQKFEOI-SSDOTTSWSA-N (5r)-5-(morpholine-4-carbonyl)pyrrolidin-2-one Chemical compound C1COCCN1C(=O)[C@H]1CCC(=O)N1 WPDJMBAXQKFEOI-SSDOTTSWSA-N 0.000 description 1
- IWMYEQSITOXBMZ-SSDOTTSWSA-N (5r)-5-(pyrrolidine-1-carbonyl)pyrrolidin-2-one Chemical compound C1CCCN1C(=O)[C@H]1CCC(=O)N1 IWMYEQSITOXBMZ-SSDOTTSWSA-N 0.000 description 1
- NDLBAWLHCCJUKI-UHFFFAOYSA-N 2-[4-(5-oxopyrrolidine-2-carbonyl)piperazin-1-yl]-n-propan-2-ylacetamide Chemical compound C1CN(CC(=O)NC(C)C)CCN1C(=O)C1NC(=O)CC1 NDLBAWLHCCJUKI-UHFFFAOYSA-N 0.000 description 1
- YMQRPXBBBOXHNZ-UHFFFAOYSA-N 2-chloro-1-morpholin-4-ylethanone Chemical compound ClCC(=O)N1CCOCC1 YMQRPXBBBOXHNZ-UHFFFAOYSA-N 0.000 description 1
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
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- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- MAFJXAYWVBYUEH-UHFFFAOYSA-N n,n'-bis(4-methoxyphenyl)ethane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1NCCNC1=CC=C(OC)C=C1 MAFJXAYWVBYUEH-UHFFFAOYSA-N 0.000 description 1
- CEUVYVBWZIVIEM-UHFFFAOYSA-N n,n-dimethyl-4-(5-oxopyrrolidine-2-carbonyl)piperazine-1-carboxamide Chemical compound C1CN(C(=O)N(C)C)CCN1C(=O)C1NC(=O)CC1 CEUVYVBWZIVIEM-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 229960002195 perazine Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1135986 | 1986-01-21 | ||
| JP1136086 | 1986-01-21 | ||
| JP17516886 | 1986-07-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH675418A5 true CH675418A5 (is") | 1990-09-28 |
Family
ID=27279384
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH195/87A CH675418A5 (is") | 1986-01-21 | 1987-01-20 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5102882A (is") |
| BE (1) | BE1003248A5 (is") |
| CA (1) | CA1323874C (is") |
| CH (1) | CH675418A5 (is") |
| DE (2) | DE3744947C2 (is") |
| ES (1) | ES2002083A6 (is") |
| FR (2) | FR2597100A1 (is") |
| GB (1) | GB2185483B (is") |
| IT (1) | IT1205715B (is") |
| NL (1) | NL192304C (is") |
| SE (1) | SE503436C2 (is") |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5021439A (en) * | 1988-10-31 | 1991-06-04 | Takeda Chemical Industries, Ltd. | Cerebral function ameliorating agents related to Tan-950 A |
| IT1244507B (it) * | 1991-04-11 | 1994-07-15 | Sigma Tau Ind Farmaceuti | Derivati dell'acido piroglutammico quali attivatori dei processi di apprendimento e della memoria e composizioni farmaceutiche comprendenti tali composti |
| FR2680508B1 (fr) * | 1991-08-20 | 1995-03-03 | Adir | Nouveaux composes amidiques des 1-(alcoxybenzyl)piperazines, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent. |
| EP0711554A4 (en) * | 1993-07-28 | 1997-07-23 | Nippon Shinyaku Co Ltd | ANTIDEPRESSANT |
| CA2157348A1 (en) * | 1994-09-01 | 1996-03-02 | Aventis Pharmaceuticals Inc. | 3-¬4-(1-substituted-4-piperazinyl)butyl|-4-thiazolidinone and related compounds |
| GB9420784D0 (en) * | 1994-10-14 | 1994-11-30 | Glaxo Group Ltd | Medicaments |
| US6194413B1 (en) * | 1995-11-13 | 2001-02-27 | Smithkline Beecham Corporation | Hemoregulatory compounds |
| PE20011081A1 (es) * | 2000-02-11 | 2001-10-22 | Vertex Pharma | Derivados de piperazina y piperidina |
| EP1546103B1 (en) * | 2002-10-03 | 2009-03-18 | Vertex Pharmaceuticals Incorporated | Piperazine and piperidine derivatives for treatment of neurological diseases |
| PT2121578T (pt) | 2007-01-12 | 2016-11-14 | Novartis Ag | Processo de preparação de ácido 5-bifenil-4-amino-2-metil-pentanoico |
| DE102008003828B3 (de) | 2008-01-10 | 2009-09-03 | Clariant International Limited | Verwendung von Salzen als Korrosionsinhibitoren mit erhöhter biologischer Abbaubarkeit und verminderter Toxizität und diese Salze |
| DE102008003826B4 (de) * | 2008-01-10 | 2010-07-22 | Clariant International Limited | Verwendung von Salzen als Korrosionsinhibitoren mit erhöhter biologischer Abbaubarkeit und verminderter Toxizität und diese Salze |
| MX2013002150A (es) | 2010-08-23 | 2013-04-03 | Novartis Ag | Proceso para la preparacion de intermediarios para la elaboracion de inhibidores de nep. |
| WO2016205348A1 (en) | 2015-06-15 | 2016-12-22 | The Children's Hospital Of Philadelphia | Methods of diagnosing and treating autism |
| WO2019143824A1 (en) * | 2018-01-18 | 2019-07-25 | Aevi Genomic Medicine, Inc. | Solid forms of fasoracetam |
| US11535604B2 (en) * | 2018-01-18 | 2022-12-27 | The Children's Hospital Of Philadelphia | Fasoracetam crystalline forms |
| GB202300833D0 (en) * | 2023-01-19 | 2023-03-08 | Nrg Therapeutics Ltd | Novel compounds |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3051722A (en) * | 1960-10-21 | 1962-08-28 | Lakeside Lab Inc | 5-pyrrolidone-2-carboxamides |
| JPS5015793B2 (is") * | 1972-06-07 | 1975-06-07 | ||
| JPS518266A (en) * | 1974-07-10 | 1976-01-23 | Sakai Chemical Industry Co | Piroridonjudotaino seizohoho |
| GB1492640A (en) * | 1975-07-08 | 1977-11-23 | Ucb Sa | L-pyroglutamyl-l-prolinamide |
| BE864269A (fr) * | 1977-03-03 | 1978-06-16 | Parke Davis & Co | Nouveaux n-(aminoalkyl substitue)-2-oxo-1-pyrrolidine-acetamides et procedes pour les produire |
| DE2924011C2 (de) * | 1979-06-13 | 1982-04-08 | A. Nattermann & Cie GmbH, 5000 Köln | Pyrrolidin-(2)-on-(1)-ylessigsäure-2,6,-dimethylanilid, Verfahren zur Herstellung und Arzneimittel, welche diese Verbindung enthalten |
| HU180925B (en) * | 1979-06-28 | 1983-05-30 | Richter Gedeon Vegyeszet | Process for producing tripeptide-amides trh-analogues,effectives on the central nerve systhem |
| JPS56147766A (en) * | 1980-04-17 | 1981-11-16 | Sakai Chem Ind Co Ltd | Preparation of lactam |
| DE3031118A1 (de) * | 1980-08-18 | 1982-04-01 | Meditest Institut für medizinisch-pharmazeutische Untersuchungen GmbH & Co KG, 7958 Laupheim | N,n'-bis(5-oxo-1-methyl-pyrrolidin-2-yl-essigsaeure)-hydrazid, verfahren zu dessen herstellung und seine verwendung als arzneimittel |
| HU184481B (en) * | 1981-10-02 | 1984-08-28 | Richter Gedeon Vegyeszet | Process for producing tripeptides for diminishing appetite |
| GB2130590B (en) * | 1982-11-10 | 1986-01-08 | Erba Farmitalia | Peptides |
| US4483991A (en) * | 1983-01-17 | 1984-11-20 | American Home Products Corporation | Hypotensive agents |
| US4525476A (en) * | 1983-05-26 | 1985-06-25 | Warner-Lambert Company | N-[1-oxo-3-(5-oxo-2-pyrrolidinyl)propyl]-alpha-aminoacids and derivatives as cognition activators |
| IT1172391B (it) * | 1983-12-23 | 1987-06-18 | Polifarma Spa | Composti tirpeptidici contenenti acido piroglutaminico e triptofano,procedimentio di produzione ed applicazioni terapeutiche |
| DE3420193A1 (de) * | 1984-05-30 | 1985-12-05 | Boehringer Ingelheim KG, 6507 Ingelheim | Neue substituierte pyrrolidinone, verfahren zu ihrer herstellung und arzneimittel |
-
1987
- 1987-01-16 FR FR8700485A patent/FR2597100A1/fr active Granted
- 1987-01-20 CH CH195/87A patent/CH675418A5/de not_active IP Right Cessation
- 1987-01-20 IT IT47545/87A patent/IT1205715B/it active
- 1987-01-20 NL NL8700119A patent/NL192304C/nl not_active IP Right Cessation
- 1987-01-20 DE DE3744947A patent/DE3744947C2/de not_active Expired - Fee Related
- 1987-01-20 ES ES8700128A patent/ES2002083A6/es not_active Expired
- 1987-01-20 DE DE19873701494 patent/DE3701494A1/de active Granted
- 1987-01-20 CA CA000527706A patent/CA1323874C/en not_active Expired - Fee Related
- 1987-01-20 SE SE8700203A patent/SE503436C2/xx not_active IP Right Cessation
- 1987-01-21 BE BE8700036A patent/BE1003248A5/fr not_active IP Right Cessation
- 1987-01-21 GB GB8701245A patent/GB2185483B/en not_active Expired - Fee Related
- 1987-09-28 FR FR8713376A patent/FR2613366A1/fr active Granted
-
1991
- 1991-02-26 US US07/661,523 patent/US5102882A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| FR2597100A1 (fr) | 1987-10-16 |
| BE1003248A5 (fr) | 1992-02-11 |
| SE8700203D0 (sv) | 1987-01-20 |
| GB8701245D0 (en) | 1987-02-25 |
| DE3701494A1 (de) | 1987-07-23 |
| ES2002083A6 (es) | 1988-07-01 |
| IT1205715B (it) | 1989-03-31 |
| FR2613366A1 (fr) | 1988-10-07 |
| GB2185483A (en) | 1987-07-22 |
| GB2185483B (en) | 1990-10-24 |
| NL192304C (nl) | 1997-05-07 |
| SE503436C2 (sv) | 1996-06-17 |
| SE8700203L (sv) | 1987-07-22 |
| FR2597100B1 (is") | 1994-08-19 |
| IT8747545A0 (it) | 1987-01-20 |
| US5102882A (en) | 1992-04-07 |
| CA1323874C (en) | 1993-11-02 |
| NL192304B (nl) | 1997-01-06 |
| FR2613366B1 (is") | 1994-08-19 |
| DE3744947C2 (is") | 1992-07-16 |
| NL8700119A (nl) | 1987-08-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |